SML1687

3BDO

≥98% (HPLC)

• Synonym(s): 3-Benzyl-5-((2-nitrophenoxy)methyl)-dihydrofuran-2(3H)-one
• Empirical Formula (Hill Notation): C₁₈H₁₇NO₅
• CAS Number: 890405-51-3
• Molecular Weight: 327.33
• UNSPSC Code: 12352200
• PubChem Substance ID: 329826016
• NACRES: NA.32

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: oil
• color: colorless to light brown
• storage temp.: 2-8°C
• SMILES string: O=C1OC(COC2=C([N+]([O-])=O)C=CC=C2)CC1CC3=CC=CC=C3
• InChI: 1S/C18H17NO5/c20-18-14(10-13-6-2-1-3-7-13)11-15(24-18)12-23-17-9-5-4-8-16(17)19(21)22/h1-9,14-15H,10-12H2

Description

Application

3BDO has been used to investigate the potential effects of metformin on inflammatory lung injury.

Biochem/physiol Actions

3BDO is a cell-permeable, orally bioavailable, non-toxic butyrolactone derivative that is shown to competitively bind FKBP1A (FK506-binding protein 1A, 12 kDa) in a reversible manner, and suppress autophagy via the mTOR pathway. 3BDO inhibits both LPS- and oxLDL-induced autophagy in HUVECs, increases TIA1 phosphorylation, and reduces autophagosomes number. It is reported to be brain permeant, and significantly decreases atherosclerosis development in apoE-/- mice (100 mg/kg, q.d., p.o.). 3BDO increases IDE and neprilysin levels, lowers amyloid-β deposition in an AβPP/PS1 transgenic mouse model of Alzheimer′s disease, and alleviates memory deficits.

An orally bioavailable, brain-permeant suppressor of mTOR-mediated autophagy; reduces Aβ levels and prevents cognitive deficits in AβPP/PS1 mouse model.
3-benzyl-5-[(2-nitrophenoxy) methyl]-dihydrofuran-2 (3H)-one (3BDO) blocks rise in LC3-II stimulated by uric acid (UA). It protects the capability of Rheb1-deficient macrophages to perform phagocytosis. 3BDO also prevents the inhibitory effects of EX-527 on eukaryotic translation initiation factor-binding protein 1(4E-BP1) phosphorylation.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable